EP0124482B1 - Imidazolides et leur emploi comme durcisseurs pour des polyépoxydes - Google Patents

Imidazolides et leur emploi comme durcisseurs pour des polyépoxydes Download PDF

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Publication number
EP0124482B1
EP0124482B1 EP84810192A EP84810192A EP0124482B1 EP 0124482 B1 EP0124482 B1 EP 0124482B1 EP 84810192 A EP84810192 A EP 84810192A EP 84810192 A EP84810192 A EP 84810192A EP 0124482 B1 EP0124482 B1 EP 0124482B1
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EP
European Patent Office
Prior art keywords
imidazolide
methyl
hydrogen
isopropyl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP84810192A
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German (de)
English (en)
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EP0124482A3 (en
EP0124482A2 (fr
Inventor
Rolf Dr. Schmid
Helmut Dr. Zondler
Michael Dr. Fischer
Werner Stauffer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hexcel Corp
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Ciba Geigy AG
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Publication date
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Publication of EP0124482A2 publication Critical patent/EP0124482A2/fr
Publication of EP0124482A3 publication Critical patent/EP0124482A3/de
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Publication of EP0124482B1 publication Critical patent/EP0124482B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/44—Amides

Definitions

  • the present invention relates to new imidazolides (N-acylimidazoles), a process for their preparation and their use as hardeners for polyepoxide compounds with an average of more than one epoxy group in the molecule.
  • imidazoles as hardeners in the curing of epoxy resins.
  • JP Auslegeschrift 49-7599 N-acylimidazoles which can carry halogen atoms, ether, thioether, cyclohexyl or unsubstituted or substituted by an ester or amide group on the imidazole ring, such as e.g. 1- (2-chlorobenzoyl) imidazole and trimethylbenzoylimidazole, as hardeners.
  • Mixtures of polyepoxides with such imidazolides can be stored for some time at room temperature with the exclusion of water and can be cured at elevated temperature by taking up water vapor from the air.
  • New imidazolides have now been found, which u. a. characterized by very good hardening with an open surface, combined with improved stability properties and longer processing times.
  • R 5 , R 6 and R 7 are a phenyl substituted by methyl or ethyl groups, 2-methylphenyl, 2-ethylphenyl, 2,6-diethylphenyl and 2,4,6-trimethylphenyl are suitable.
  • Imidazolides of the formula I are preferred in which R 1 , R 2 and R 3 are methyl and R 4 is hydrogen.
  • imidazolides of the formula I in which one of the symbols R s , R 6 and R 7 is an unsubstituted phenyl and the other two are hydrogen. Particularly preferred are those in which R 5 is phenyl, R 6 and R 7 are hydrogen.
  • the compound 1- (2,4,6-trimethylbenzoyl) -2-phenylimidazole is particularly preferred.
  • the imidazolides of the formula I according to the invention can be obtained, for example, by adding an acid halide of the formula II with an imidazole of the formula III where X corresponds to chlorine or bromine, and the symbols R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the abovementioned meaning, in the presence of an acid acceptor.
  • the commonly used substances such as. B. tertiary amines, especially triethylamine, pyridine bases, or the imidazole of the formula III can be used in molar excess.
  • Aromatic hydrocarbons such as toluene or xylene are suitable as solvents; halogenated aliphatic or aromatic hydrocarbons, such as CCl 4 , HCCI 3 , CH 2 Cl 2 ; Ethylene chloride or chlorobenzene, dichlorobenzene or chloronaphthalene; Ethers such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran.
  • Aromatic hydrocarbons such as toluene or xylene are suitable as solvents; halogenated aliphatic or aromatic hydrocarbons, such as CCl 4 , HCCI 3 , CH 2 Cl 2 ; Ethylene chloride or chlorobenzene, dichlorobenzene or chloronaphthalene; Ethers such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran.
  • the reaction is expediently carried out in the temperature range from 0 ° C. to 150 ° C.
  • the acid halides and imidazoles used as starting compounds are commercially available or can be prepared by known methods.
  • the imidazolides according to the invention are outstandingly suitable as hardeners for epoxy resins.
  • the present invention therefore furthermore relates to curable mixtures which comprise at least one imidazolide of the formula I and a polyepoxide compound having on average more than one epoxide group in the molecule.
  • the mixing ratio can be chosen so that the curable mixtures contain 2 to 15 parts by weight of imidazolide of the formula I per 100 parts by weight of polyepoxide compound.
  • the curable mixture particularly preferably contains a bisphenol A diglycidyl ether, a polyglycidyl ether of phenol or cresol novolaks or an N-glycidyl compound, in particular N, N, N ', N'-tetraglycidyl-bis- (p-aminophenyl) as the polyepoxide compound.
  • the hardenable mixtures according to the invention are preferably cured to give moldings and the like in a temperature interval of 50 ° -250 ° C., preferably between 100 ° and 200 ° C.
  • the curing can also be carried out in two or more stages in a known manner, the first curing stage being carried out at low temperature and the post-curing at higher temperature, preferably at temperatures which correspond to the glass transition temperature of the fully cured resin.
  • Suitable curing catalysts are e.g. aliphatic alcohols and phenols, preferably polyhydric phenolic compounds such as bisphenol A and pyrogallol.
  • polyepoxides, as listed under a) and e), which still contain free hydroxyl groups, is particularly advantageous.
  • the catalysts can be used in amounts of 1 to 12% by weight, preferably 3 to 8% by weight, based on the reaction mixture.
  • the curable mixtures according to the invention can furthermore be mixed in any phase with conventional modifiers, such as extenders, fillers and reinforcing agents, pigments, dyes, organic solvents, plasticizers, leveling agents, thixotropic agents, flexibilizers, flame retardants or mold release agents.
  • conventional modifiers such as extenders, fillers and reinforcing agents, pigments, dyes, organic solvents, plasticizers, leveling agents, thixotropic agents, flexibilizers, flame retardants or mold release agents.
  • coal tar As extenders, reinforcing agents, fillers and pigments that can be used in the curable mixtures according to the invention, for. B. called: coal tar, bitumen, liquid coumarone indene resins, textile fibers, glass fibers, asbestos fibers, boron fibers, carbon fibers, cellulose, polyethylene powder, polypropylene powder, quartz powder, mineral silicates, such as mica, asbestos powder, slate flour, kaolin, silica gelatin gelatin, gelatine , Titanium dioxide, carbon black, graphite, oxide paints, such as iron oxide, or metal powder, such as aluminum powder or iron powder.
  • Suitable organic solvents for the modification of the curable mixtures are e.g. Toluene, xylene, butyl acetate, acetone and methyl ethyl ketone.
  • plasticizers for the modification of the curable mixtures e.g. Dibutyl, dioctyl and dinonyl phthalate, tricresyl phosphate, trixylenyl phosphate and diphenoxyethyl formal can be used.
  • a leveling agent when using the curable mixtures especially in surface protection, one can e.g. Add silicones, liquid acrylic resins, cellulose acetobutyrate, polyvinyl butyral, waxes, stearates, etc. (some of which are also used as mold release agents).
  • the curable mixtures according to the invention can be prepared in a customary manner with the aid of known mixing units (stirrers, kneaders, rollers or in the case of solid substances or powders in mills or dry mixers). In some cases, the mixture must be warmed up briefly to achieve sufficient homogeneity.
  • the curable mixtures according to the invention are notable for good storage stability, long processing times, high heat resistance, good resistance to hot water and chemicals, good heat resistance and good curing even with open curing in a thin layer.
  • the curable mixtures according to the invention are used above all in the fields of surface protection, electrical engineering, lamination processes, adhesive technology and in construction. They can be used in formulations adapted to the specific application, in the unfilled or filled state, if appropriate in the form of solutions or emulsions, as paints, solvent-free coatings, sintered powders, molding compounds, injection-molding formulations, immersion resins, casting resins, foams, films, films, binders, tooling resins, Laminating resins, sealing and leveling compounds, flooring compounds and binders for mineral aggregates can be used.
  • the curable mixtures according to the invention are particularly advantageously used as winding or impregnating resins for fiber-reinforced composites, such as for the production of hot water-resistant pipes and containers, as a matrix component for high-quality composites and for bonding plastics, composites and metals.
  • the high glass transition temperature is a Measure of the good hardening with an open surface.
  • the resin-hardener mixture also shows a dynamic viscosity of 210 mPa ⁇ s at 75 ° C. After 8 hours at 75 ° C, the viscosity only increases up to 350 mPa ⁇ s.
  • the system is therefore particularly suitable for use as an impregnation resin, and it hardens at moderately high temperatures (mostly at 140 ° C).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Resins (AREA)

Claims (10)

1. Imidazolides répondant à la formule I:
Figure imgb0013
 dans laquelle:
R1 représente un radical méthyle, éthyle ou isopropyle,
R2, R3 et R4 représentent chacun, indépendamment les uns des autres, l'hydrogène ou un radical méthyle, éthyle ou isopropyle, avec la condition que R2 ne soit l'hydrogène que dans le cas où R, est un radical isopropyle, et
R5, R6 et R7 représentent chacun, indépendamment les uns des autres, l'hydrogène, un radical méthyle, éthyle ou isopropyle, ou un radical phényle non substitué ou porteur de radicaux méthyles ou éthyles, avec la condition qu'au moins un des symboles Rs, Re et R7 représente un phényle non substitué ou substitué conformément à la définition.
2. Imidazolides selon la revendication 1 dans lesquels R1, R2 et R3 représentent chacun un méthyle et R4 représente l'hydrogène.
3. Imidazolides selon la revendication 1 dans lesquels un des symboles Rs, R6 et R7 représente un phényle non substitué et les deux autres représentent chacun l'hydrogène.
4. Imidazolides selon la revendication 1 dans lesquels R5 représente un phényle, et R6 et R7 représentent chacun l'hydrogène.
5. Imidazolide selon la revendication 1, en l'espèce le (triméthyl-2,4,6 benzoyl)-1 phényl-2 imidazole.
6. Procédé pour préparer des imidazolides de formule I selon la revendication 1, procédé caractérisé en ce qu'on fait réagir un halogénure d'acide de formule II:
Figure imgb0014
avec un imidazole de formule III:
Figure imgb0015
formules dans lesquelles X représente le chlore ou le brome, et les symboles R1, R2, R3, R4, R5, R6 et R7 ont les significations qui leur ont été attribuées à la revendication 1, en présence d'un accepteur d'acides.
7. Mélanges durcissables qui contiennent au moins un imidazolide de formule I selon la revendication 1 et un composé polyépoxydique renfermant en moyenne plus d'un radical époxy par molécule.
8. Mélanges durcissables selon la revendication 7 qui contiennent, comme composé polyépoxydique, un éther diglycidylique du bis-phénol A, un éther polyglycidylique d'une novolaque phénolique ou crésolique, ou un composé N-glycidyli- que.
9. Mélanges durcissables selon la revendication 7 dans lesquels l'imidazolide est le (triméthyl-2,4,6 benzoyl)-1 phényl-2 imidazole.
10. Produits que l'on a obtenus par durcissement en utilisant un mélange selon la revendication 7.
EP84810192A 1983-04-29 1984-04-19 Imidazolides et leur emploi comme durcisseurs pour des polyépoxydes Expired EP0124482B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH231683 1983-04-29
CH2316/83 1983-04-29

Publications (3)

Publication Number Publication Date
EP0124482A2 EP0124482A2 (fr) 1984-11-07
EP0124482A3 EP0124482A3 (en) 1987-05-13
EP0124482B1 true EP0124482B1 (fr) 1989-11-08

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EP84810192A Expired EP0124482B1 (fr) 1983-04-29 1984-04-19 Imidazolides et leur emploi comme durcisseurs pour des polyépoxydes

Country Status (5)

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US (2) US4587311A (fr)
EP (1) EP0124482B1 (fr)
JP (1) JPS59206361A (fr)
CA (1) CA1220483A (fr)
DE (1) DE3480392D1 (fr)

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CN108291011B (zh) 2015-09-09 2021-03-02 卡本有限公司 用于增材制造的环氧双重固化树脂
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EP3255039B1 (fr) 2016-06-10 2018-12-12 Evonik Degussa GmbH Procede de fabrication de 2-(2, 2, 6, 6 - tetramethylpiperidine-4-yl) propane-1,3-diamine
ES2702751T3 (es) 2016-06-10 2019-03-05 Evonik Degussa Gmbh 2-(3-(aminometil)-3,5,5-trimetilciclohexil)propan-1,3-diamina, un procedimiento de preparación y uso
EP3255079B1 (fr) 2016-06-10 2018-08-15 Evonik Degussa GmbH Composition epoxyde contenant 2-(3, 3, 5-trimethylcyclohexyl) propane -1, 3 diamine en tant que durcisseur
EP3255078B1 (fr) 2016-06-10 2018-08-15 Evonik Degussa GmbH Composition epoxyde contenant 2-(2, 2, 6, 6-tretramethylhylpiperidine-4-yl) propane -1,3 diamine en tant que durcisseur
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WO2018148632A1 (fr) 2017-02-13 2018-08-16 Carbon, Inc. Procédé de fabrication d'objets composites par fabrication additive
WO2018165090A1 (fr) 2017-03-09 2018-09-13 Carbon, Inc. Polymères haute température résistants produits par stéréolithographie
EP3592558A1 (fr) 2017-03-23 2020-01-15 Carbon, Inc. Supports de lèvres utiles pour la fabrication d'objets par fabrication additive
EP3600842B1 (fr) 2017-03-27 2022-04-20 Carbon, Inc. Procédé de fabrication d'objets tridimensionnels par fabrication additive
EP3849806B1 (fr) 2018-09-10 2023-04-05 Carbon, Inc. Résines à double polymérisation pour fabrication additive pour la production d'objets ignifuges
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Also Published As

Publication number Publication date
US4587311A (en) 1986-05-06
CA1220483A (fr) 1987-04-14
EP0124482A3 (en) 1987-05-13
JPH0570625B2 (fr) 1993-10-05
US4628105A (en) 1986-12-09
DE3480392D1 (en) 1989-12-14
JPS59206361A (ja) 1984-11-22
EP0124482A2 (fr) 1984-11-07

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